When It Rayns, It Pours

A man reflects on his tattered past while chasing a passion for music through the avenue of his local nightlife shuttle service.

  • Bailey McDonald
  • Riley Goll
  • Austin Pluskot
  • Bailey McDonald
  • Bailey McDonald
  • Bailey McDonald
  • Project Type:
    Documentary, Short
  • Runtime:
    7 minutes 3 seconds
  • Completion Date:
    July 4, 2023
  • Production Budget:
    0 USD
  • Country of Origin:
    United States
  • Country of Filming:
    United States
  • Language:
  • Shooting Format:
  • Aspect Ratio:
  • Film Color:
  • First-time Filmmaker:
  • Student Project:
    Yes - University of Florida
Director Biography - Bailey McDonald

Bailey McDonald is a documentary filmmaker from Orlando, Florida. He graduated from the School of Art and Art History at the University of Florida with a BFA in Photography and is currently pursuing his MFA in Film Production with a concentration in cinematography at Florida State University's College of Motion Picture Arts.

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Director Statement

When It Rayns, It Pours is a short documentary film centered around an aspiring musician under the alias, “Rayn”. What started as a conversation on a Gainesville street corner with the saxophone-playing party bus driver snowballed into a film that explores self-perception and overcoming fear.

Ryan Sheppard (Rayn) has been frequently documented in the local news, making appearances on behalf of his exotic nightlife shuttle service. The more I researched Rayn's story, however, the more I realized that there was a prevailing theme over the media coverage and his public perception: those stories tended to make a spectacle of Rayn’s unconventional lifestyle. Once I had a chance to sit down and talk with Rayn, I realized that this story needed to be about the “why” behind his actions.

Employing both cinema verité and illustrative filmmaking styles, the work toes the line between representation and abstraction. At times, the camera is loose and observational, echoing a representation found in cinema verité. At others, the film pulls from aesthetics of film noir, favoring oblique lines and low-key night scenes to create visual dissonance that works in tandem with Rayn’s reality.

At the center of this film is a struggle with fear; fear to be remembered, fear to be favored, fear to be loved. Ryan’s story teaches that fear is oftentimes the only obstacle in the way of pursuing our passions, and that the path to triumph that fear is by leading a life of love.